US11680051B2ActiveUtilityA1

Crystalline forms of 3-substituted 1,2,4-oxadiazole

98
Assignee: AURIGENE DISCOVERY TECH LTDPriority: Oct 11, 2017Filed: Aug 30, 2021Granted: Jun 20, 2023
Est. expiryOct 11, 2037(~11.3 yrs left)· nominal 20-yr term from priority
Inventors:Pottayil Govindan Nair SasikumarSeetharamaiah Setty Sudarshan Naremaddepalli
C07D 271/06C07B 2200/13A61K 31/4245A61P 37/02A61P 35/00A61P 29/00A61P 37/06A61P 31/00A61P 31/18A61P 31/14A61P 31/20
98
PatentIndex Score
6
Cited by
156
References
31
Claims

Abstract

The invention relates to crystalline forms of a 3-substituted 1,2,4-oxadiazole compound, methods of their preparation, and related pharmaceutical preparations thereof. The invention also relates to preparations suitable for pharmaceutical, veterinary, and agriculturally-relevant uses.

Claims

exact text as granted — not AI-modified
The invention claimed is: 
     
       1. A method for preparing a crystalline compound having the structure of formula 
       
         
           
           
               
               
           
         
       
       comprising:
 a) providing a mixture comprising a compound of formula (I) and a solvent; 
 b) crystallizing the compound of formula (I) from the mixture comprising the compound of formula (I); and 
 
       wherein, prior to step a), the compound of formula (I) is in a solution and step a) comprises contacting the solution with vapor of the solvent, thereby forming the mixture of step a). 
     
     
       2. The method of  claim 1 , wherein the solution is prepared by filtering a suspension comprising compound of formula (I), thereby forming the solution. 
     
     
       3. The method of  claim 1 , wherein the solvent is selected from acetonitrile, anisole, dichloromethane, ethanol, isopropyl acetate, methyl tert-butyl ether (MTBE), n-heptane, tetrahydrofuran, water, and mixtures thereof. 
     
     
       4. The method of  claim 1 , wherein the purity of the crystalline compound is selected from about 90%, about 91%, about 92%, about 93%, about 94%, about 95%, about 96%, about 97%, about 98%, and about 99%. 
     
     
       5. The crystalline compound of  claim 1 , wherein the crystalline compound is a solvate. 
     
     
       6. The method of  claim 1 , wherein the crystalline compound is a hydrate. 
     
     
       7. The method of  claim 1 , wherein the crystalline compound is a monohydrate. 
     
     
       8. The method of  claim 1 , wherein the crystalline compound has 2θ values 8.4±0.2, 13.6±0.2, 16.5±0.2, 16.8±0.2, 21.4±0.2, and 28.4±0.2. 
     
     
       9. The method of  claim 1 , wherein the crystalline compound has 2θ values 8.4±0.2, 13.6±0.2, 16.5±0.2, 16.8±0.2, 19.3±0.2, 20.4±0.2, 21.4±0.2, and 28.4±0.2. 
     
     
       10. The method of  claim 1 , wherein the crystalline compound has 2θ values 8.4±0.2, 13.6±0.2, 16.5±0.2, 16.8±0.2, 19.3±0.2, 19.9±0.2, 20.4±0.2, 21.4±0.2, 24.5±0.2, 26.5±0.2, and 28.4±0.2. 
     
     
       11. The method of  claim 1 , wherein the crystalline compound has 2θ values 8.4±0.2, 11.5±0.2, 13.6±0.2, 16.5±0.2, 16.8±0.2, 19.3±0.2, 19.9±0.2, 20.4±0.2, 21.4±0.2, 21.8±0.2, 24.5±0.2, 26.5±0.2, 27.5±0.2, 28.0±0.2, 28.4±0.2, 30.0±0.2, and 32.4±0.2. 
     
     
       12. The method of  claim 1 , wherein the crystalline compound has an XRD pattern substantially as shown in  FIG.  1   . 
     
     
       13. The method of  claim 1 , wherein the crystalline compound has 2θ values of 6.8±0.2, 8.4±0.2, 10.0±0.2, 10.6±0.2, 11.5±0.2, 13.6±0.2, 16.5±0.2, 16.8±0.2, 17.6±0.2, 18.8±0.2, 19.3±0.2, 19.9±0.2, 20.4±0.2, 20.6±0.2, 21.00±0.2, 21.4±0.2, 21.8±0.2, 22.6±0.2, 23.6±0.2, 24.5±0.2, 24.8±0.2, 25.3±0.2, 26.5±0.2, 27.1±0.2, 27.5±0.2, 28.0±0.2, 28.4±0.2, 29.3±0.2, 30.1±0.2, 30.8±0.2, 31.5±0.2, 32.4±0.2, 33.0±0.2, 33.5±0.2, 34.3±0.2, 35.3±0.2, 36.5±0.2, 37.6±0.2, 38.1±0.2, and 38.7±0.2. 
     
     
       14. The method of  claim 1 , wherein the crystalline compound has 2θ values of 10.9±0.2, 11.6±0.2, 12.9±0.2, 13.5±0.2, 15.7±0.2, 16.1±0.2, 17.0±0.2, 19.6±0.2, 19.6±0.2, 20.3±0.2, 21.1±0.2, 21.4±0.2, 22.2±0.2, 22.9±0.2, 24.2±0.2, 24.5±0.2, 24.8±0.2, 25.1±0.2, 25.8±0.2, 26.2±0.2, 26.4±0.2, 27.2±0.2, 28.2±0.2, 28.9±0.2, 29.7±0.2, 30.2±0.2, 31.0±0.2, 32.2±0.2, 33.7±0.2, 34.2±0.2, 36.0±0.2, 37.0±0.2, 38.4±0.2, and 39.0±0.2. 
     
     
       15. A method for preparing a crystalline compound having the structure of formula (I): 
       
         
           
           
               
               
           
         
       
       comprising exposing a solid form of the compound of formula (I) to vapor of a solvent, thereby obtaining the crystalline compound. 
     
     
       16. The method of  claim 15 , wherein the solvent is selected from acetonitrile, anisole, dichloromethane, ethanol, isopropyl acetate, methyl tert-butyl ether (MTBE), n-heptane, tetrahydrofuran, water, and mixtures thereof. 
     
     
       17. The method of  claim 15 , wherein the purity of the crystalline compound is selected from about 90%, about 91%, about 92%, about 93%, about 94%, about 95%, about 96%, about 97%, about 98%, and about 99%. 
     
     
       18. The method of  claim 15 , wherein the compound is solvated. 
     
     
       19. The method of  claim 15 , wherein the crystalline compound is a hydrate. 
     
     
       20. The method of  claim 15 , wherein the crystalline compound is a monohydrate. 
     
     
       21. The method of  claim 15 , wherein the crystalline compound has 2θ values 8.4±0.2, 13.6±0.2, 16.5±0.2, 16.8±0.2, 21.4±0.2, and 28.4±0.2. 
     
     
       22. The method of  claim 15 , wherein the crystalline compound has 2θ values 8.4±0.2, 13.6±0.2, 16.5±0.2, 16.8±0.2, 19.3±0.2, 20.4±0.2, 21.4±0.2, and 28.4±0.2. 
     
     
       23. The method of  claim 15 , wherein the crystalline compound has 2θ values 8.4±0.2, 13.6±0.2, 16.5±0.2, 16.8±0.2, 19.3±0.2, 19.9±0.2, 20.4±0.2, 21.4±0.2, 24.5±0.2, 26.5±0.2, and 28.4±0.2. 
     
     
       24. The method of  claim 15 , wherein the crystalline compound has 2θ values of 8.4±0.2, 11.5±0.2, 13.6±0.2, 16.5±0.2, 16.8±0.2, 19.3±0.2, 19.9±0.2, 20.4±0.2, 21.4±0.2, 21.8±0.2, 24.5±0.2, 26.5±0.2, 27.5±0.2, 28.0±0.2, 28.4±0.2, 30.0±0.2, and 32.4±0.2. 
     
     
       25. The method of  claim 15 , wherein the crystalline compound has an XRD pattern substantially as shown in  FIG.  1   . 
     
     
       26. The method of  claim 15 , wherein the crystalline compound has 2θ values of 6.8±0.2, 8.4±0.2, 10.0±0.2, 10.6±0.2, 11.5±0.2, 13.6±0.2, 16.5±0.2, 16.8±0.2, 17.6±0.2, 18.8±0.2, 19.3±0.2, 19.9±0.2, 20.4±0.2, 20.6±0.2, 21.00±0.2, 21.4±0.2, 21.8±0.2, 22.6±0.2, 23.6±0.2, 24.5±0.2, 24.8±0.2, 25.3±0.2, 26.5±0.2, 27.1±0.2, 27.5±0.2, 28.0±0.2, 28.4±0.2, 29.3±0.2, 30.1±0.2, 30.8±0.2, 31.5±0.2, 32.4±0.2, 33.0±0.2, 33.5±0.2, 34.3±0.2, 35.3±0.2, 36.5±0.2, 37.6±0.2, 38.1±0.2, and 38.7±0.2. 
     
     
       27. The method of  claim 15 , wherein the crystalline compound has 2θ values of 10.9±0.2, 11.6±0.2, 12.9±0.2, 13.5±0.2, 15.7±0.2, 16.1±0.2, 17.0±0.2, 19.1±0.2, 19.6±0.2, 20.3±0.2, 21.1±0.2, 21.4±0.2, 22.2±0.2, 22.9±0.2, 24.2±0.2, 24.5±0.2, 24.8±0.2, 25.1±0.2, 25.8±0.2, 26.2±0.2, 26.4±0.2, 27.2±0.2, 28.2±0.2, 28.9±0.2, 29.7±0.2, 30.2±0.2, 31.0±0.2, 32.2±0.2, 33.7±0.2, 34.2±0.2, 36.0±0.2, 37.0±0.2, 38.4±0.2, and 39.0±0.2. 
     
     
       28. A crystalline compound having the structure of formula (I): 
       
         
           
           
               
               
           
         
       
       and 2θ values of 6.8±0.2, 8.4±0.2, 10.0±0.2, 10.6±0.2, 11.5±0.2, 13.6±0.2, 16.5±0.2, 16.8±0.2, 17.6±0.2, 18.8±0.2, 19.3±0.2, 19.9±0.2, 20.4±0.2, 20.6±0.2, 21.00±0.2, 21.4±0.2, 21.8±0.2, 22.6±0.2, 23.6±0.2, 24.5±0.2, 24.8±0.2, 25.3±0.2, 26.5±0.2, 27.1±0.2, 27.5±0.2, 28.0±0.2, 28.4±0.2, 29.3±0.2, 30.1±0.2, 30.8±0.2, 31.5±0.2, 32.4±0.2, 33.0±0.2, 33.5±0.2, 34.3±0.2, 35.3±0.2, 36.5±0.2, 37.6±0.2, 38.1±0.2, and 38.7±0.2. 
     
     
       29. The crystalline compound of  claim 28 , wherein the purity of the crystalline compound is selected from about 90%, about 91%, about 92%, about 93%, about 94%, about 95%, about 96%, about 97%, about 98%, and about 99%. 
     
     
       30. A crystalline compound having the structure of formula (I): 
       
         
           
           
               
               
           
         
       
       and 2θ values of 10.9±0.2, 11.6±0.2, 12.9±0.2, 13.5±0.2, 15.7±0.2, 16.1±0.2, 17.0±0.2, 19.1±0.2, 19.6±0.2, 20.3±0.2, 21.1±0.2, 21.4±0.2, 22.2±0.2, 22.9±0.2, 24.2±0.2, 24.5±0.2, 24.8±0.2, 25.1±0.2, 25.8±0.2, 26.2±0.2, 26.4±0.2, 27.2±0.2, 28.2±0.2, 28.9±0.2, 29.7±0.2, 30.2±0.2, 31.0±0.2, 32.2±0.2, 33.7±0.2, 34.2±0.2, 36.0±0.2, 37.0±0.2, 38.4±0.2, and 39.0±0.2. 
     
     
       31. The crystalline compound of  claim 30 , wherein the purity of the crystalline compound is selected from about 90%, about 91%, about 92%, about 93%, about 94%, about 95%, about 96%, about 97%, about 98%, and about 99%.

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